Vacation before resignation - when to give notice?

Question

I am in a bit of a pickle. I have been looking for a new job for almost 2 months. I will be leaving the country for 2 weeks on vacation, March 1st-15th. My plan was to line up a job, give resignation notice such that my final day is February 28th, go have a blast in Europe, and then return home to relocate to my new job. There are many points in play here that inform and/or complicate the situation:

• I have not yet received an offer for a new job.
• I have not notified my boss of my vacation plans.
• I only have 4 days of PTO.
• I am able dip into negative PTO (they will just deduct any balance from my final paycheck).
• My boss will be on vacation February 10th-20th. I don't want to ruin his vacation.
• I will need to use at least 1 of my PTO days for a final job interview.
• I cannot extend my resignation period by using PTO, or I cannot use PTO during my 2 weeks notice period (I will look at the exact wording of this policy tomorrow).
• I have worked here for 2.5 years and I have a great relationship with my manager.

Options

I have come up with three options. The first two are risky because I would be giving a resignation notice without having a job offer. In the third, I avoid giving notice, but my behavior may give it away anyways!

Leave and Cleave

Notify my boss on February 9th that my last day will be February 28th.

Divide and Conquer

Notify my boss on February 20th that my last day will be March 22nd (do the math: 1 week, vacation, 1 week). My boss gets to enjoy his vacation, and I mine; I might even have a job offer by this point! This could optionally be extended to the end of March.

Tight Lipped

Notify my boss ASAP that I am going on vacation. This option kind of hinders my ability to take yet another vacation day between now and March 1st for an interview. I may even end up tipping my hand. Even 30 days is not much notice for a 2 week vacation, and to add to that I might be putting in a resignation notice shortly after I get back. This one kind of leaves a bad taste in my mouth.

The Question

Which of these options is the most logical? Are there other options that I haven't considered? I am aware that this could be seen as opinion-based, but I would really appreciate some other ideas and input. I have to say, writing this out as a question has already helped me a great deal. Being forced to describe the situation caused me to formulate my thoughts into some actually cohesive, tangible options.

I'm sorry if you consider this a duplicate. I have seen similar questions on here, but none that I felt described my same situation enough.

Answer 1

You don't have a job offer until you have a written job offer with a start date, and you have passed all required background and reference checks. So unless you have some funds saved up and wouldn't mind a month or six of funemployment, do not resign without a job offer. Do not even let them know you're thinking of leaving.

If you've already gone ahead and booked your travel plans, you're just going to have to have to tell your boss you're going dip into those un-paid PTO days. Tell your boss now before he plans a big project for early March.

When you get interviews, tell your coworkers you have an emergency dental appointment. No one should ask for more details . . .if they do, just say it's gross and painful and you don't want to talk about it at work.

You'd be surprised how little people notice when you stay vague on the details.

While it's kind of you to think of your boss's vacation, you should consider that it's only a couple of weeks away, and you haven't had this final interview yet. Unless you're in a very high-demand industry, you probably won't have this lined up until after your vacation. Remember, most companies will make you negotiate the signing offer, do references and background checks, all of which can add a week+ to your time waiting to get your official start date and clear to resign.

But at the off chance that worst happens and you are ready to resign while your boss is on vacation, plan to ask your new company if you can start on the 22nd or the 29th of March. This way, you can ask your manager if they'd like you to return to the office for that second week. There is a good chance that they will appreciate the offer but not take you up on it.

The two week standard is usually offered but not always accepted. Some companies will, in some circumstances, simply cut a check for two weeks and march the leaving employee out the door within a half an hour. If it's a small company and you have a lot of hands-on client relationships, they might want more time to transfer that information. But if you're a salesperson, they will have no reason to keep you on for a day longer than when you gave notice. It really depends on the company and your position, so double check the HR policy on notice.

Answer 2

I appreciate the comments and the answer that was added, but I wanted to go ahead and add an answer of my own to explain what I ended up doing. I hope it helps someone down the road.

I talked to my boss before he left for his vacation and told him I was leaving. While he was sad to lose me, he understood completely. He told me that he's been expecting me to leave since I started (it is a small, boring city and anyone can tell I'm more of a big city person). Anyways, I put in my two weeks notice and everyone is sending me off with the best of wishes.

As I have shared the news with people, I have been open about the fact that I don't have a job offer yet. Many of my colleagues have offered to reach out to their contacts in other companies and locations. As it turns out, I now have several solid leads on both coasts. One of them is a close friend of a colleague, and is actually pretty excited to make me a job offer.

Obviously, these results are very unique to the situation, and the relationships you have with your boss and your coworkers. My advice to someone in the same situation would be to assess your relationships; try to ascertain if people would be happy for you for advancing your career or mad at you for leaving them. If it is the former, consider telling someone close to you (that you can trust not to share this information). Their contacts and network may just be the key to the opportunity that you are seeking.